1. Inspector/structural engineer... Did you have the home inspected before buying? Egress is easy enough to figure out on your own.

Then, an energy auditor. Ask your local utility if they have a program/relationship for energy auditors.

Go from there with a general contractor (if you are adding dormers, might need the structural engineer again) to do the work and/or roofer for skylights (solatubes would also be an option.)

Also if you add window area or skylights, you cooling needs may drastically change in the space. Consider those implications as well.

Yes, the changes in cooling and ventilation (and the possible decisions about how structural and even architectural changes can alter those needs) are exactly what's making it hard to determine where to start.

We did have a thorough inspection done when buying the house. At that point we were focused on the present condition of the place, so I didn't even think to ask about what we'd need to do when we were ready to punch in a few more windows/dormers/skylights.

Thanks for the advice! I just need to take a deep breath and make that first phone call . . .

"Who should we call first? General contractors? Structural engineers? Architects? The guy who fixed our friend's garage door?"

You might want to visit your local building department and ask them a few questions first.

They can give you a list of the contractors who are registered with the city.

They aren't allowed to refer a specific one, but at least you will know that the ones on file are more likely to do things right (to code).

I did this after a bogus referral to a contractor who wanted to do things without pulling permits.

You can select a qualified contractor and ask for advice and prices but that gets difficult if you want to bid the work. To do that you need to do the design work and documentation first. It is simpler but more expensive to hire an architect and do everything in a logical sequence. I can't guess about the need for professional assistance because I don't know much about the existing conditions. Perhaps the first step would be to hire a contractor to investigate and document the existing conditions, then decide if you need professional design assistance.

Start with the money tree first. ;)

Then hire an architect who specializes in renovations to coordinate the project. It might be more cost effective to remove the entire roof and start over than it would to piecemeal the project. Older Capes find it problematic to get the code required R-value in above the living space without doing all spray in foam, and that can get really expensive quickly. At that point, tearing off the roof and reframing the second floor becomes cheaper. It's pretty much always easier to do than trying to cut in a patchwork here and there. Look on posts here from EngineerChic who just did that very thing to her cape. It was in the $130K range for final costs if I recall, but your costs may vary due to the condition of the home and your location.

rather than hiring a utility sponsored rater or
auditor check with resnet or bpi for
someone in your area. better have the rater/auditor
as independent working for you than subsidised by
utility company.

best of luck.